JP6588966B2 - Ａｍｐタンパク質キナーゼ作動薬としてのアザベンゾイミダゾール誘導体 - Google Patents
Ａｍｐタンパク質キナーゼ作動薬としてのアザベンゾイミダゾール誘導体 Download PDFInfo
- Publication number
- JP6588966B2 JP6588966B2 JP2017507411A JP2017507411A JP6588966B2 JP 6588966 B2 JP6588966 B2 JP 6588966B2 JP 2017507411 A JP2017507411 A JP 2017507411A JP 2017507411 A JP2017507411 A JP 2017507411A JP 6588966 B2 JP6588966 B2 JP 6588966B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- phenyl
- methyl
- groups
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Links
- 0 ***c1c(*)cc2[n]c(O*)nc2n1 Chemical compound ***c1c(*)cc2[n]c(O*)nc2n1 0.000 description 6
- VUTUQIZPZBFOIX-UHFFFAOYSA-O CC(C)(C(C)(C)O[B+]c(cc1)ccc1[NH3+])O Chemical compound CC(C)(C(C)(C)O[B+]c(cc1)ccc1[NH3+])O VUTUQIZPZBFOIX-UHFFFAOYSA-O 0.000 description 1
- LPEBIPBZRMFNPZ-JXZFBBMPSA-N CC(C)NS(C)(=Nc(cc1)ccc1-c(cc1)ccc1-c(nc1[nH]c(/[O]=C(\C[O]=C23)/[C@H]2OC[C@H]3O)nc1c1)c1Cl)=O Chemical compound CC(C)NS(C)(=Nc(cc1)ccc1-c(cc1)ccc1-c(nc1[nH]c(/[O]=C(\C[O]=C23)/[C@H]2OC[C@H]3O)nc1c1)c1Cl)=O LPEBIPBZRMFNPZ-JXZFBBMPSA-N 0.000 description 1
- HWIOSAAXDBYOJD-VIWCIXJMSA-N CC1(C)OB(c(cc2)ccc2-c(nc2[n](COCC[Si+](C)(C)C)c(O[C@H](COC34)C3OC[C@H]4O)nc2c2)c2Cl)OC1(C)C Chemical compound CC1(C)OB(c(cc2)ccc2-c(nc2[n](COCC[Si+](C)(C)C)c(O[C@H](COC34)C3OC[C@H]4O)nc2c2)c2Cl)OC1(C)C HWIOSAAXDBYOJD-VIWCIXJMSA-N 0.000 description 1
- MFAJKMJWAOTWRY-UHFFFAOYSA-N CCCCNCC1C=CC(Br)=CC1 Chemical compound CCCCNCC1C=CC(Br)=CC1 MFAJKMJWAOTWRY-UHFFFAOYSA-N 0.000 description 1
- ZPZFGVZYNKYSHJ-QBYJUEORSA-N CCCOC[n]1c(OC(CO)C(C2C)OC[C@H]2O)nc2cc(Cl)c(-c3ccc(B4OC(C)(C)C(C)(C)O4)cc3)nc12 Chemical compound CCCOC[n]1c(OC(CO)C(C2C)OC[C@H]2O)nc2cc(Cl)c(-c3ccc(B4OC(C)(C)C(C)(C)O4)cc3)nc12 ZPZFGVZYNKYSHJ-QBYJUEORSA-N 0.000 description 1
- RTBPGZXZXBTDKG-HKGREKTFSA-N CCN(C)S(C)(=Nc(cc1)ccc1-c(cc1)ccc1-c(nc1[nH]c(OC(CO[C@@H]23)[C@H]2OC[C@H]3O)nc1c1)c1Cl)=O Chemical compound CCN(C)S(C)(=Nc(cc1)ccc1-c(cc1)ccc1-c(nc1[nH]c(OC(CO[C@@H]23)[C@H]2OC[C@H]3O)nc1c1)c1Cl)=O RTBPGZXZXBTDKG-HKGREKTFSA-N 0.000 description 1
- RAXNVEDKFAPYLX-YPRZIUAMSA-N CN(C)S(C)(=Nc(cc1)ccc1-c(nc1[n](COCC[Si+](C)(C)C)c(O[C@H](COC23)[C@H]2OC[C@H]3O)nc1c1)c1Cl)=O Chemical compound CN(C)S(C)(=Nc(cc1)ccc1-c(nc1[n](COCC[Si+](C)(C)C)c(O[C@H](COC23)[C@H]2OC[C@H]3O)nc1c1)c1Cl)=O RAXNVEDKFAPYLX-YPRZIUAMSA-N 0.000 description 1
- IOOMUSKIEGNGCG-UHFFFAOYSA-O CN(C)S(C)([NH2+]c(cc1)ccc1Br)=O Chemical compound CN(C)S(C)([NH2+]c(cc1)ccc1Br)=O IOOMUSKIEGNGCG-UHFFFAOYSA-O 0.000 description 1
- AZWWBIYERFDTLU-UHFFFAOYSA-N CN(C)[O]=S(c(cc1)ccc1Br)=NC(C(F)(F)F)=O Chemical compound CN(C)[O]=S(c(cc1)ccc1Br)=NC(C(F)(F)F)=O AZWWBIYERFDTLU-UHFFFAOYSA-N 0.000 description 1
- IKGMIRQEXATIQO-UHFFFAOYSA-N CN(CCC1)S1(=NC)=O Chemical compound CN(CCC1)S1(=NC)=O IKGMIRQEXATIQO-UHFFFAOYSA-N 0.000 description 1
- AMOIZCPQDVYFIM-FQMOWQLGSA-N CN/[S-3]=N\c(cc1)ccc1-c(cc1)ccc1-c(nc1[nH]c(OC(CO[C@@H]23)[C@H]2OC[C@H]3O)nc1c1)c1Cl Chemical compound CN/[S-3]=N\c(cc1)ccc1-c(cc1)ccc1-c(nc1[nH]c(OC(CO[C@@H]23)[C@H]2OC[C@H]3O)nc1c1)c1Cl AMOIZCPQDVYFIM-FQMOWQLGSA-N 0.000 description 1
- GBABZZGCPXJIAQ-WYFSRSOLSA-N CNS(C)(=Nc(cc1)ccc1-c(cc1)ccc1-c(nc1[nH]c(O[C@H](CO[C@@H]23)C2OC[C@H]3O)nc1c1)c1Cl)=O Chemical compound CNS(C)(=Nc(cc1)ccc1-c(cc1)ccc1-c(nc1[nH]c(O[C@H](CO[C@@H]23)C2OC[C@H]3O)nc1c1)c1Cl)=O GBABZZGCPXJIAQ-WYFSRSOLSA-N 0.000 description 1
- UGGKYDXFUQRSIY-XZNFVCIBSA-N CNS(c(cc1)ccc1-c(cc1)ccc1-c(nc1[n](COCC[Si+](C)(C)C)c(OC(COC23)[C@H]2OC[C@H]3O)nc1c1)c1Cl)(=NC)=O Chemical compound CNS(c(cc1)ccc1-c(cc1)ccc1-c(nc1[n](COCC[Si+](C)(C)C)c(OC(COC23)[C@H]2OC[C@H]3O)nc1c1)c1Cl)(=NC)=O UGGKYDXFUQRSIY-XZNFVCIBSA-N 0.000 description 1
- VDECMIFVFCVQBU-UHFFFAOYSA-N CNS(c(cc1)ccc1Br)=O Chemical compound CNS(c(cc1)ccc1Br)=O VDECMIFVFCVQBU-UHFFFAOYSA-N 0.000 description 1
- SPPGHSUNEBADNG-UHFFFAOYSA-N CNS(c(cc1)ccc1[Br]=C)(=NC)=O Chemical compound CNS(c(cc1)ccc1[Br]=C)(=NC)=O SPPGHSUNEBADNG-UHFFFAOYSA-N 0.000 description 1
- OUZCROLKVCFZIF-UHFFFAOYSA-N CS(=Nc(cc1)ccc1-c(cc1)ccc1-c(nc1[nH]c(OC(COC23)C2OCC3O)nc1c1)c1Cl)=O Chemical compound CS(=Nc(cc1)ccc1-c(cc1)ccc1-c(nc1[nH]c(OC(COC23)C2OCC3O)nc1c1)c1Cl)=O OUZCROLKVCFZIF-UHFFFAOYSA-N 0.000 description 1
- CEFMGULURYKWCT-UHFFFAOYSA-N CS(Nc(cc1)ccc1Br)(N1CCCC1)=O Chemical compound CS(Nc(cc1)ccc1Br)(N1CCCC1)=O CEFMGULURYKWCT-UHFFFAOYSA-N 0.000 description 1
- IXNICKWMYNPXLN-UHFFFAOYSA-N CS(Nc(cc1)ccc1Br)=O Chemical compound CS(Nc(cc1)ccc1Br)=O IXNICKWMYNPXLN-UHFFFAOYSA-N 0.000 description 1
- LUKJSRYUAZFSJD-AAVRWANBSA-N C[Si+](C)CCOC[n](c1n2)c(O[C@H](CO[C@@H]34)[C@H]3OC[C@H]4O)nc1cc(Cl)c2I Chemical compound C[Si+](C)CCOC[n](c1n2)c(O[C@H](CO[C@@H]34)[C@H]3OC[C@H]4O)nc1cc(Cl)c2I LUKJSRYUAZFSJD-AAVRWANBSA-N 0.000 description 1
- GEVBQBLZEOJJHV-MPVIZJAMSA-N C[Si](C)(C)CCOC[n]1c(O[C@H](CO[C@@H]23)C2OC[C@H]3O)nc2cc(Cl)c(-c(cc3)ccc3-c(cc3)ccc3N=S(C)(N3CCCC3)=O)nc12 Chemical compound C[Si](C)(C)CCOC[n]1c(O[C@H](CO[C@@H]23)C2OC[C@H]3O)nc2cc(Cl)c(-c(cc3)ccc3-c(cc3)ccc3N=S(C)(N3CCCC3)=O)nc12 GEVBQBLZEOJJHV-MPVIZJAMSA-N 0.000 description 1
- DDBKUQGLWANCEA-UHFFFAOYSA-N O=C(C(F)(F)F)NS(c(cc1)ccc1Br)=O Chemical compound O=C(C(F)(F)F)NS(c(cc1)ccc1Br)=O DDBKUQGLWANCEA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14180549.9 | 2014-08-11 | ||
| EP14180549 | 2014-08-11 | ||
| PCT/EP2015/067900 WO2016023789A1 (en) | 2014-08-11 | 2015-08-04 | Azabenzimidazole derivatives as amp protein kinase agonistes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017523226A JP2017523226A (ja) | 2017-08-17 |
| JP2017523226A5 JP2017523226A5 (enExample) | 2018-09-20 |
| JP6588966B2 true JP6588966B2 (ja) | 2019-10-09 |
Family
ID=51298659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017507411A Active JP6588966B2 (ja) | 2014-08-11 | 2015-08-04 | Ａｍｐタンパク質キナーゼ作動薬としてのアザベンゾイミダゾール誘導体 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US9422312B2 (enExample) |
| EP (1) | EP3180338B1 (enExample) |
| JP (1) | JP6588966B2 (enExample) |
| WO (1) | WO2016023789A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2015309863B2 (en) | 2014-08-27 | 2019-12-05 | Shionogi & Co., Ltd. | Azaindole derivative having AMPK-activating effect |
| AU2015338042A1 (en) | 2014-10-28 | 2017-04-27 | Shionogi & Co., Ltd. | Heterocyclic derivative having AMPK activating effect |
| WO2017146186A1 (ja) | 2016-02-26 | 2017-08-31 | 塩野義製薬株式会社 | Ａｍｐｋ活性化作用を有する５－フェニルアザインドール誘導体 |
| EP3459949A4 (en) * | 2016-05-20 | 2020-04-08 | Shionogi & Co., Ltd | 5-SUBSTITUTED BENZIMIDAZOLE DERIVATIVE AND 5-SUBSTITUTED AZABENZIMIDAZOLE DERIVATIVE WITH AMPK ACTIVATION EFFECT |
| UY37659A (es) | 2017-04-10 | 2018-10-31 | Phenex Fxr Gmbh | Moduladores del receptor x del hígado (lxr) |
| AU2021275038A1 (en) | 2020-05-19 | 2022-12-22 | Kallyope, Inc. | AMPK activators |
| CN113717087A (zh) * | 2020-05-26 | 2021-11-30 | 瑞博(杭州)医药科技有限公司 | 一种脱氧氟化试剂的制备方法 |
| CA3183575A1 (en) | 2020-06-26 | 2021-12-30 | Iyassu Sebhat | Ampk activators |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013520502A (ja) * | 2010-02-25 | 2013-06-06 | メルク・シャープ・エンド・ドーム・コーポレイション | 有用な抗糖尿病薬である新規な環状ベンズイミダゾール誘導体 |
| CN103209981B (zh) * | 2010-09-10 | 2016-12-28 | 盐野义制药株式会社 | 具有ampk活化作用的杂环稠合咪唑衍生物 |
| SG192941A1 (en) * | 2011-02-25 | 2013-09-30 | Merck Sharp & Dohme | Novel cyclic azabenzimidazole derivatives useful as anti-diabetic agents |
| EP2888006B1 (en) * | 2012-08-22 | 2019-04-24 | Merck Sharp & Dohme Corp. | Novel azabenzimidazole tetrahydropyran derivatives useful as ampk activators |
| PL3022210T3 (pl) * | 2013-07-17 | 2018-08-31 | Boehringer Ingelheim International Gmbh | Nowy pochodne azabenzimidazolu |
-
2015
- 2015-08-04 JP JP2017507411A patent/JP6588966B2/ja active Active
- 2015-08-04 WO PCT/EP2015/067900 patent/WO2016023789A1/en not_active Ceased
- 2015-08-04 EP EP15747465.1A patent/EP3180338B1/en active Active
- 2015-08-10 US US14/822,268 patent/US9422312B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2017523226A (ja) | 2017-08-17 |
| US9422312B2 (en) | 2016-08-23 |
| US20160039846A1 (en) | 2016-02-11 |
| EP3180338A1 (en) | 2017-06-21 |
| EP3180338B1 (en) | 2018-05-09 |
| WO2016023789A1 (en) | 2016-02-18 |
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